Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality

Selective monohydrogenation of an achiral ferrocenebis(enal) was achieved with a resin‐supported peptide catalyst to afford an enantioenriched planar‐chiral product. It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality w...

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Veröffentlicht in:	European journal of organic chemistry 2015-06, Vol.2015 (18), p.3894-3898
Hauptverfasser:	Akagawa, Kengo, Akiyama, Midori, Kudo, Kazuaki
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Sprache:	eng
Schlagworte:	Asymmetric catalysis Desymmetrization Organocatalysis Peptides Planar chirality
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container_title	European journal of organic chemistry
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creator	Akagawa, Kengo Akiyama, Midori Kudo, Kazuaki
description	Selective monohydrogenation of an achiral ferrocenebis(enal) was achieved with a resin‐supported peptide catalyst to afford an enantioenriched planar‐chiral product. It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality was induced on an achiral ferrocenyl compound by peptide‐catalyzed desymmetrization. Although such an asymmetric reaction could not be realized with a low‐molecular‐weight catalyst, a resin‐supported peptide with a turn structure afforded products in a highly enantioselective manner.
doi_str_mv	10.1002/ejoc.201500428
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It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality was induced on an achiral ferrocenyl compound by peptide‐catalyzed desymmetrization. Although such an asymmetric reaction could not be realized with a low‐molecular‐weight catalyst, a resin‐supported peptide with a turn structure afforded products in a highly enantioselective manner.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201500428</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Asymmetric catalysis ; Desymmetrization ; Organocatalysis ; Peptides ; Planar chirality</subject><ispartof>European journal of organic chemistry, 2015-06, Vol.2015 (18), p.3894-3898</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH & Co. 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J. Org. Chem</addtitle><description>Selective monohydrogenation of an achiral ferrocenebis(enal) was achieved with a resin‐supported peptide catalyst to afford an enantioenriched planar‐chiral product. It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality was induced on an achiral ferrocenyl compound by peptide‐catalyzed desymmetrization. Although such an asymmetric reaction could not be realized with a low‐molecular‐weight catalyst, a resin‐supported peptide with a turn structure afforded products in a highly enantioselective manner.</description><subject>Asymmetric catalysis</subject><subject>Desymmetrization</subject><subject>Organocatalysis</subject><subject>Peptides</subject><subject>Planar chirality</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LxDAQhosouH5cPQc8d50kbdocl7ofirgelIqXENMJdu02Ne2i9ddbXVm8eZp34Hlm4A2CMwpjCsAucOXMmAGNASKW7gUjClKGICTsDzniUUglfzwMjtp2BQBSCDoK1B02XVlgmOlOV_0nFuQS2369xs6Xn7orXU2cJbomE_NSel2RGXrvDNZ9RTK3btymLsi9I1d1sTFI7ipda0-yH7bs-pPgwOqqxdPfeRw8zKb32SK8Wc6vsslNaGJB0_A5KWwqDBep5cKgLRgwWcCw0lgz-YwsZphYbhNDmTSFTRhKjqhTKRORMH4cnG_vNt69bbDt1MptfD28VFSkMhUConSgxlvKeNe2Hq1qfLnWvlcU1HeJ6rtEtStxEORWeC8r7P-h1fR6mf11w61bth1-7FztX5VIeBKr_Hau8hzkUx4vVM6_AMm6hiQ</recordid><startdate>201506</startdate><enddate>201506</enddate><creator>Akagawa, Kengo</creator><creator>Akiyama, Midori</creator><creator>Kudo, Kazuaki</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201506</creationdate><title>Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality</title><author>Akagawa, Kengo ; Akiyama, Midori ; Kudo, Kazuaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5618-b7df86c368f36cefd2029d068f15a29be252e7f3f7c129cdf72e93eea89976723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Asymmetric catalysis</topic><topic>Desymmetrization</topic><topic>Organocatalysis</topic><topic>Peptides</topic><topic>Planar chirality</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Akagawa, Kengo</creatorcontrib><creatorcontrib>Akiyama, Midori</creatorcontrib><creatorcontrib>Kudo, Kazuaki</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Akagawa, Kengo</au><au>Akiyama, Midori</au><au>Kudo, Kazuaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. 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subjects	Asymmetric catalysis Desymmetrization Organocatalysis Peptides Planar chirality
title	Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality
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